DE2201584A1 - Substituierte Azabicycloalkane - Google Patents
Substituierte AzabicycloalkaneInfo
- Publication number
- DE2201584A1 DE2201584A1 DE19722201584 DE2201584A DE2201584A1 DE 2201584 A1 DE2201584 A1 DE 2201584A1 DE 19722201584 DE19722201584 DE 19722201584 DE 2201584 A DE2201584 A DE 2201584A DE 2201584 A1 DE2201584 A1 DE 2201584A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- formula
- decahydroquinoline
- chloro
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004480 active ingredient Substances 0.000 claims description 52
- -1 thiocarbonic acid halide Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 57
- 150000002148 esters Chemical class 0.000 description 44
- 241000196324 Embryophyta Species 0.000 description 32
- 239000004202 carbamide Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241000209094 Oryza Species 0.000 description 21
- 235000007164 Oryza sativa Nutrition 0.000 description 19
- 235000009566 rice Nutrition 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000006072 paste Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 241001148683 Zostera marina Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 235000013877 carbamide Nutrition 0.000 description 7
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 235000007238 Secale cereale Nutrition 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940035893 uracil Drugs 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- POTIYWUALSJREP-DTWKUNHWSA-N (4as,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCC[C@@H]2CCCC[C@H]21 POTIYWUALSJREP-DTWKUNHWSA-N 0.000 description 2
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical class N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 2
- ZLRUVRUSTQTGGS-UHFFFAOYSA-N 1-(2,3,3a,4,5,6,7,7a-octahydroindol-1-yl)propane-1-thione Chemical compound C(C)C(=S)N1CCC2CCCCC12 ZLRUVRUSTQTGGS-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- 240000004296 Lolium perenne Species 0.000 description 2
- 241000209049 Poa pratensis Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000209056 Secale Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002191 fatty alcohols Chemical group 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 229940055764 triaz Drugs 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 229940066528 trichloroacetate Drugs 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- POTIYWUALSJREP-RKDXNWHRSA-N (4ar,8ar)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCC[C@H]2CCCC[C@H]21 POTIYWUALSJREP-RKDXNWHRSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- ALCHNIFNFKJBDW-UHFFFAOYSA-N 1-(2-methyl-3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)propane-1-thione Chemical compound C1CCCC2N(C(=S)CC)C(C)CCC21 ALCHNIFNFKJBDW-UHFFFAOYSA-N 0.000 description 1
- MDLKWDQMIZRIBY-UHFFFAOYSA-N 1-(dimethylamino)ethanol Chemical class CC(O)N(C)C MDLKWDQMIZRIBY-UHFFFAOYSA-N 0.000 description 1
- QZEKHJXYZSJVCL-UHFFFAOYSA-N 2,2,3-trichloropropanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCl QZEKHJXYZSJVCL-UHFFFAOYSA-N 0.000 description 1
- OBLYWUBMZGHQDN-UHFFFAOYSA-N 2,2-dichlorobutanoic acid Chemical compound CCC(Cl)(Cl)C(O)=O OBLYWUBMZGHQDN-UHFFFAOYSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- RORFIYBSDKQWBH-UHFFFAOYSA-N 2-chloro-2-phenoxypropanoic acid Chemical compound OC(=O)C(Cl)(C)OC1=CC=CC=C1 RORFIYBSDKQWBH-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- AOWXSXDTSFEHMV-UHFFFAOYSA-N 2-ethoxy-4,6-dinitrophenol Chemical compound CCOC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O AOWXSXDTSFEHMV-UHFFFAOYSA-N 0.000 description 1
- SYWMIOFIFBKHTK-UHFFFAOYSA-N 2-ethyl-4,6-dinitrophenol Chemical compound CCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O SYWMIOFIFBKHTK-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH55371A CH535011A (de) | 1971-01-14 | 1971-01-14 | Selektive herbizide Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2201584A1 true DE2201584A1 (de) | 1972-07-27 |
Family
ID=4189652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722201584 Pending DE2201584A1 (de) | 1971-01-14 | 1972-01-13 | Substituierte Azabicycloalkane |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3776912A (hu) |
| AT (1) | AT315567B (hu) |
| BE (1) | BE777997A (hu) |
| CA (1) | CA994781A (hu) |
| CH (4) | CH535011A (hu) |
| CS (1) | CS176181B2 (hu) |
| DD (1) | DD100859A5 (hu) |
| DE (1) | DE2201584A1 (hu) |
| EG (1) | EG11289A (hu) |
| ES (1) | ES398822A1 (hu) |
| FR (1) | FR2121834B1 (hu) |
| GB (1) | GB1345672A (hu) |
| HU (1) | HU163471B (hu) |
| IL (1) | IL38497A (hu) |
| IT (1) | IT946560B (hu) |
| NL (1) | NL7200533A (hu) |
| OA (1) | OA04064A (hu) |
| PH (1) | PH9356A (hu) |
| RO (1) | RO61543A (hu) |
| SU (1) | SU555828A3 (hu) |
| ZA (1) | ZA72227B (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002461A (en) * | 1969-07-16 | 1977-01-11 | Ciba-Geigy Corporation | Substituted 2-azabicycloalkanes as selective herbicides |
| CH533106A (de) * | 1971-01-14 | 1973-01-31 | Ciba Geigy Ag | Verfahren zur Herstellung von substituierten Azabicycloalkanen |
| US4292237A (en) * | 1977-11-14 | 1981-09-29 | The B. F. Goodrich Company | Polymeric ultraviolet light stabilizers containing hindered alkyl amines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3344134A (en) * | 1964-04-29 | 1967-09-26 | Monsanto Co | Azabicyclononanecarbothiolates |
| CH510380A (de) * | 1969-04-29 | 1971-07-31 | Ciba Geigy Ag | Verwendung von Dithiocarbamaten zur Beeinflussung der Pflanzenentwicklung |
| FI49164C (fi) * | 1969-07-16 | 1975-04-10 | Agripat Sa | Herbisideissä käytettäviä substituoituja 2-atsabisykloalkaaneja. |
-
1971
- 1971-01-11 OA OA54460A patent/OA04064A/xx unknown
- 1971-01-14 CH CH55371A patent/CH535011A/de not_active IP Right Cessation
- 1971-01-14 CH CH1519072A patent/CH533108A/de not_active IP Right Cessation
- 1971-01-14 CH CH1519172A patent/CH533109A/de not_active IP Right Cessation
- 1971-01-14 CH CH603672A patent/CH533107A/de not_active IP Right Cessation
- 1971-12-30 DD DD160048A patent/DD100859A5/xx unknown
-
1972
- 1972-01-03 IL IL38497A patent/IL38497A/xx unknown
- 1972-01-05 CA CA131,708A patent/CA994781A/en not_active Expired
- 1972-01-10 US US00216778A patent/US3776912A/en not_active Expired - Lifetime
- 1972-01-12 EG EG17/72A patent/EG11289A/xx active
- 1972-01-13 BE BE777997A patent/BE777997A/xx unknown
- 1972-01-13 HU HUAI205A patent/HU163471B/hu unknown
- 1972-01-13 CS CS227A patent/CS176181B2/cs unknown
- 1972-01-13 FR FR7201134A patent/FR2121834B1/fr not_active Expired
- 1972-01-13 IT IT19346/72A patent/IT946560B/it active
- 1972-01-13 NL NL7200533A patent/NL7200533A/xx unknown
- 1972-01-13 GB GB170372A patent/GB1345672A/en not_active Expired
- 1972-01-13 DE DE19722201584 patent/DE2201584A1/de active Pending
- 1972-01-13 ZA ZA720227A patent/ZA72227B/xx unknown
- 1972-01-13 RO RO7200069385A patent/RO61543A/ro unknown
- 1972-01-13 PH PH13194*UA patent/PH9356A/en unknown
- 1972-01-13 AT AT26572A patent/AT315567B/de not_active IP Right Cessation
- 1972-01-13 ES ES398822A patent/ES398822A1/es not_active Expired
- 1972-01-14 SU SU1737351A patent/SU555828A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU555828A3 (ru) | 1977-04-25 |
| CS176181B2 (hu) | 1977-06-30 |
| CH535011A (de) | 1973-03-31 |
| BE777997A (fr) | 1972-07-13 |
| AT315567B (de) | 1974-05-27 |
| ZA72227B (en) | 1972-09-27 |
| EG11289A (en) | 1977-01-31 |
| HU163471B (hu) | 1973-09-27 |
| US3776912A (en) | 1973-12-04 |
| CH533108A (de) | 1973-01-31 |
| PH9356A (en) | 1975-10-06 |
| CH533107A (de) | 1973-01-31 |
| IL38497A0 (en) | 1972-03-28 |
| IT946560B (it) | 1973-05-21 |
| NL7200533A (hu) | 1972-07-18 |
| GB1345672A (en) | 1974-01-30 |
| OA04064A (fr) | 1979-10-30 |
| ES398822A1 (es) | 1975-06-16 |
| FR2121834B1 (hu) | 1978-03-03 |
| IL38497A (en) | 1975-02-10 |
| CA994781A (en) | 1976-08-10 |
| FR2121834A1 (hu) | 1972-08-25 |
| CH533109A (de) | 1973-01-31 |
| DD100859A5 (hu) | 1973-10-12 |
| RO61543A (hu) | 1977-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |